Benzyl Bromide → 1-benzyl-3-chloro-5-methoxypyridazin-4(1H)-one

HRID 333724Notes

Reaction equation

HRID 333724 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:13]([N:4]1[CH:5]=[C:6]([O:9][CH3:10])[C:7](=[O:8])[C:2]([Cl:1])=[N:3]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178493809HCID 178493809, compound

Product 1

HCID 866865601-benzyl-3-chloro-5-methoxypyridazin-4(1H)-oneYield 126.8%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Chloro-5-methoxypyridazin-4-ol (10.0 g) was dissolved in N,N-dimethylformamide (300 mL), sodium hydride (3.26 g, 55 wt %) and tetrabutylammonium iodide (4.60 g) were added at 0° C., and the mixture was stirred at the same temperature for 10 min. To the reaction mixture was added benzyl bromide (12.3 g) at 0° C., and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with water, and extracted with dichloromethane. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated. Recrystallization of the residue from ethyl acetate/hexane gave the title compound (19.8 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. extractionextracted with dichloromethane
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customRecrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-59950978c44444f7b957c7ddf24a5b57
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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